Wingman
by snaptrapper
Summary: When Fishlegs asks Hiccup to be his wingman for a date with Heather, he is totally against the idea, but when he finds out that his high school crush is going to be there things take a different turn to what he was expecting [Modern AU] [Hiccstrid]
1. Chapter 1

When Fishlegs asks Hiccup to be his wingman for a date with Heather, he is totally against the idea, but when he finds out that his high school crush is going to be there things take a different turn to what he was expecting **[Modern AU] [Hiccstrid]**

When Hiccup agreed to meet Fishlegs for a coffee in Berk's only Starbuck's he thought it would be the usual, play a game of 'Maces and Talons' and have a couple of coffees over the game, boy was he wrong.

"Fishlegs, the last time I've seen you this nervous was when you got married to Ruffnut in a school play and had to kiss her. In fact, I still have the video of when you fainted during the play, when you were meant to kiss her." I said with a laugh at that memory.

"Nervous me? I'm not nervous at all." Replied Fishlegs, as they both ordered are usual drinks; Fishlegs a hot chocolate and myself a latte.

"So, what's the problem this time? Parents are coming around? Family party? Meatlug gone to the vets again?" Meatlug, was Fishlegs' dog, a large sausage dog to be precise.

"Parents were here last weekend and no thanks for your concern but now that Meatlug is on a strict diet and getting plenty of walks, she's fine. How's Toothless?" asked Fishlegs.

"Oh, he's fine. He hasn't lost any more legs. If that's what you were wondering." Toothless, was my three-legged cat, he lost his left leg in a car crash and I found him in a cat shelter and took him in, we've been inseparable ever since. "Anyway, stop trying to change the subject what the problem?"

After a period of silence, I asked again, "Fishy, what's the matter?"

"I've got a date" said Fishlegs.

"So, let me get this straight, you've got a date?" I asked. "Well congrats, good for you mate."

We then moved on to are usual table, by the window, over-looking the town. From here you could see all of Berk, including the Town Hall, where my Dad spent most of his time, due to being the Mayor of Berk.

"So, who is the lucky lady to have a date with the mighty Fishlegs?" We set out the board for the start of the game and it was my turn to go first.

"Heather." Was the reply from my friend.

"Heather, as in Dagur's younger sister?" Dagur, was a strange man and for some reason called me his 'brother', but, he was a family friend and a well-known person across the archipelago. He was the son, of the mayor of Berserk, a near by city. Me and him go long-back to when we were just kids messing around at the annual meetings between the two mayors.

"Yep, that one" replied Fishlegs, who was moving swiftly around the board with his pieces, trying to claim the piece of my chief, but a solid defensive positioning from my men protected him.

"How and when did this happen?" I asked, as I moved some of pieces on to the offensive.

"Well, to be honest I'm not sure where I got the courage to make it happen. It was almost like a superior alter ego took over and stepped up to ask her." Fishlegs continued to take the attack to my defence but to no prevail. "I've seen her a couple of times in the pet shop when I was collecting food for Meatlug. And Mrs Jones had to go and make a phone call about delivery's or something, leaving me and her just there. And after a while we got talking about our pets and I asked her out for a date."

"Wow. So when is it, your date?" I asked. Fishlegs attacking strategy had left him in the open, I just needed a few more turns to gather enough support, before I could launch a full-scale attack on his Chief.

"Friday. And here's the thing she said to bring a friend." Said Fishlegs with a hopeful look in his eyes.

"Me? You want me to be your wingman?" I asked as I started to mount my attack.

"Yes, I do. I mean its not like your going to be doing anything on Friday are you?"

"I am." I said. "Don't you raise that eyebrow at me Ingerman, me and Toothless have plans of binge watching some tv program or something."

"C'mon Hiccup, I need your help. I can't exactly use Snotlout or Tuffnut could I? Snotlout, would just be Snotlout and Tuffnut would probably blow something up. Neither of them would help me impress Heather and you already know her, so it'll be fine." Replied Fishlegs, as he managed to take one of my pieces.

"Fair point." I am too well aware of the damage Snotlout or Tuffnut could do. "Ok so I'll be your third wheel then, lurking in the background getting bad pictures for your wedding in the future."

"Oh no, you won't be third wheeling. Heather is also bringing a friend."

"Please don't let that be Ruffnut" I begged.

"No, I think your like who it is."

"And who would that be then Fishlegs?" I asked as I began to sweep in on another victory.

"Astrid Hofferson." Stated Fishlegs. You, see Astrid Hofferson was my high-school crush and in fact despite not being at Berk University like the rest of the gang. She got a scholarship at 'Defenders of the Wing University to study Sport Science with Heather. "This is your chance to rekindle the one-sided romance you had" laughed Fishlegs.

"There was no romance between me and her, there were hardly any conversations between me and her. It was like she avoided me like a dragon would an eel." I said

"Nonsense, she was just going through a tough time, her Uncle had died in that house fire. They called him 'Fireman Fearless Finn' and she drifted away from everyone, not just you. Its part of the reason she went to 'Defenders of the Wing Uni' and not Berk Uni."

"Fishlegs, I really think this is a bad idea. You're win her over without me being there." I said, trying to suggest to Fishlegs another idea.

"The chance of me 'winning' her over increase by a tenth-fold if I have a wingman." Responded Fishlegs with a sly grin.

"Ok, fine I'll do it" I said as I swiftly moved my pieces into place to claim victory. "Good game, but you left yourself open to be flanked. Let me know the details for Friday ok?" I asked.

"Thank Thor, I didn't want to have to ask Snotlout or Tuffnut, that would be a disaster. And of course, though I don't know what were doing yet, but I'll let you know."

We then said are goodbyes and parted ways to go to our respective homes. It was all a bit mad to think in a few days he was basically going on a date with Astrid Hofferson after so long.

On the other side of town, Heather was having a similar conversation with Astrid.

"C'mon Astrid. It'll be good for you and the guy is quite cute as well." Said Heather.

"OK fine, its only one night and I guess if it means that you'll stop bugging me about it I'll do it, as long as its not Snotlout or Tuffnut." Replied Astrid

"No, it's not neither of them, but don't worry you'll be in good hands and company I know it."

"Who is it? C'mon you can tell me, I know you can. I know you want to" said Astrid as she tried to persuade her friend for a name.

"Nah, I'm not saying anything. It'll be a surprise" grinned Heather, knowing to well that Astrid was going to behead her with her axe when she finds out who it is.

 **So that's the wrap on chapter 1, let me know what you think of it in the reviews or any improvements that could be made to it.**

 **As for the next chapter probably, sometime this forthcoming week.**


	2. Chapter 2

_**AN: A Reviewer notified me that my storey has similarities to Harrypanther's recent Valentine's day fic and I have since spoken to him and he has said its fine that the tittle and original idea to the storey are similar, though there are differences in the stories.**_

 _ **Also, thanks for the reviews people, keep them coming in with improvements that could be made and your thoughts on the storey. So, I've tried to keep to a 3**_ _ **rd**_ _ **person perspective during this chapter.**_

 _ **As for updating, I was thinking Sunday or Mondays weekly as I'm at uni and time is of the essence with exams approaching soon again.**_

When Hiccup got a text from Fishlegs that he should call him during his lunch break, he thought it would be about Fishlegs' date and what restaurant they would be going to or maybe fashion advice on what colour tie to wear, not that they would be spending an hour and a half rock climbing on Friday evening.

"I'm not I can really do this, Fishlegs. I mean have you ever seen a one-legged man do rock climbing?" asked Hiccup to his friend when he found out what they would be doing for the evening. "I was sought of expecting a nice sit-down restaurant, where I couldn't embarrass myself too much y'know."

"It'll be fine Hiccup and anyway I let Heather choose what she would like to do." Replied Fishlegs.

"Can you even rock climb Fishlegs?" questioned Hiccup as he began to tuck into his home-made sandwiches by the River Eel, inaptly named for its mythical eel's that once roamed in the river.

"Well, no. But I've never tried, so statistically the chances of a human being able to rock climb are 67.56%."

"How do you even know that stuff? And do you know the chance of a one-legged man being able to rock climb? Asked Hiccup as he opened his packet of crisps.

"No, but I'm sure Astrid won't let you get injured to badly anyway" replied Fishlegs.

"Not helping Fishlegs. Anyway, is there a plan for after Rock climbing?"

"Yeah we're going to this diner a couple of minutes' walk away from it. There's changing rooms and showers at the rock climbing so bring clothes to change into for afters. Do you mind picking me and the girls up on Friday?" asked Fishlegs.

"Ok, smart casual I assume? And yeah I'll pick you and the girls up on Friday as well." Hiccup and Fishlegs said their goodbyes and Hiccup headed back to work.

Friday evening had arrived too early for Hiccup's likening, was he ready to meet his high-school crush again after all this time? He sat on the edge of his bed playing through several scenario's in his head of how the evening would play out, though some of them unrealistic but amusing to think of. What if Astrid fell off the wall and needed the kiss of life? What if his metal leg, fell off half way up the wall? How would he get down and how embarrassing it would be for everyone else if he was no good at it or couldn't do it at all?

Packing a rucksack with some clothes Hiccup made his way to the car and drove to Fishlegs' house. He was greeted by Fishlegs and an over excited Meatlug, who thought it was a good idea to slobber all over his face before he was going out. Fishlegs was wearing some gym clothes, with a pair of sweatpants and brown gym t-shirt, whilst Hiccup was in tracksuit bottoms with a tight fitting red t-shirt to go with his green hoody.

After getting in the car and plugging in Heather's address where Astrid had agreed to meet as well. Hiccup's black BMW 220d M sport convertible lit into action and began speeding across town to Heather's address.

"Should I get out as well, or do you think its best if I stay in here?" asked Hiccup as they pulled up outside Heather's.

"Come in, I think that's better." Responded Fishlegs.

Both men then go out of the car and Fishlegs rang the doorbell. The doorbell was answered by Astrid, who herself was wearing black legging and a navy-blue gym shirt and I don't think it was physically possible for Hiccup's jaw to drop any lower than it had. The t-shirt expressed Astrid's physique and show just enough amount of soft pale skin to let Hiccup's mind drift elsewhere.

"Evening boys, do come on in. Heather's just in the bathroom finishing up. I guess you must be the mystery man Heather has told be about." Spoke Astrid as she began to let her eyes wander across the lean shape that was Hiccup. He was certainly good looking and cute, but there's a sense of familiarity in this person. Where have I seen them before? Thought Astrid.

"Err…hi Astrid…hi" muttered a shy and nervous Hiccup.

"Do I know you from somewhere? I think I recognise you" asked Astrid

"Err… I guess Heather hasn't told you who I am?" responded Hiccup, who was slowly losing the stutter in his voice and beginning to become more confident in Astrid's presence. At the shake of Astrid's head, "I'm Hiccup, Hiccup Haddock. We did go to the same school as each other, though I doubt you would remember the shy freckled kid."

"No, I remember you. You were the kid who would fall over his own feet and once set the metalwork room on fire." Replied Astrid. "Though I haven't forgiven you for what you did back then."

Hiccup looked puzzled. What did he do that could have made Astrid, so distraught and angry at him? He had never really interacted with her or spoken to her which could have put himself in this hole. Has he already ruined the slim chance of a relationship or mutual understanding between himself and Astrid all those years ago?

"Astrid, could you come and help me with something?" asked Heather who now had left the bathroom and moved onto what can only be guessed as the main bedroom.

Once, they were inside Heather asked, "So, was it a good surprise? Did I do well at matchmaking?"

"Hiccup Haddock, what were you thinking? Could you really see myself and him together?" responded Astrid in an angry whisper.

"Give the boy a chance Astrid, he's changed since school, for the better as well. At least get to know him and give him a proper chance. He deserves it and you deserve someone who would treat you right, especially after the Thuggery debacle." Explained Heather as she began to put her clothes for later and shower stuff into a bag.

"Don't mention him, that stays in the past and anyway you know I can't forgive him for what happened."

"Does he even know what he has supposedly done wrong Astrid? I don't think he knows, otherwise Hiccup would have apologised, I know he would of."

"Fine, I give him a chance, but only to please you and Fishlegs. How do you know him so well anyway?" asked Astrid.

"Family friend, him and Dagur are weirdly close. It's not something you would expect from those two." Replied Heather as they made their way back out into the hall, where Hiccup and Fishlegs then greeted Heather, before moving out to the car.

After a short drive to the rock climbing, Hiccup jumped out the car and courteously ran around to Astrid's door and opened it, with a mock bow to go with it. His actions landed him with a bruised arm after a trademark Astrid punch, with a knowing smile from Heather; Astrid wouldn't admit of course, but it looked as if there was some chemistry there after all. The last time Heather had seen Astrid punch them like that had been Thuggery, before things got ugly between them.

After filing in some health and safety forms, they made their way over to the first wall, were they sat there things down. Hiccup took this opportunity to switch legs and change into some shorts, so the leg would be easier to remove and wouldn't get caught by the tracksuits.

"Haddock, you're meant to get undressed in the bedroom, save that for Astrid later." Teased Heather, with Astrid and Hiccup beginning to blush and Astrid throwing a typical Astrid death stare at her best friend.

After, Hiccup had switched legs, they decided that the girls should go first and show them how it was done. Both girls had successfully climbed to the top of the wall and expertly climbed back down.

Now, it was the boy's turn. Hiccup and Fishlegs slowly began to make their way towards the wall and with a bit of encouragement from the girls began to climb up the wall.

"So, c'mon admit it. You like him, don't you?" asked Heather as they watched the boys climb up the wall.

"You know, I thought this was a date for you and Fishlegs, not me and Hiccup." Replied Astrid, not daring to take an eye off Hiccup.

"Oh, it is. But you two seem to be a good match for each other. Me and Fishy want are friends to be happy too." By now the boys had begun to make their descent after a relatively slow climb to the top.

They moved around the centre, onto the next walls, with each commencing wall building up in difficulty. There session was about to come to an end and it was decided that there should be a race. Heather vs Fishlegs and Astrid vs Hiccup.

Heather comfortably beat Fishlegs in their race to the top of the wall and now it was Astrid vs Hiccup.

Both of them were competitive and eager to win. Astrid had the better start, but Hiccup and his long limbs easily caught up, but the one thing Hiccup had wanted not to happen did.

'Clonk'

That was the sound of an expensive carbon fibre leg, designed by Hiccup himself falling to the ground and leaving Hiccup half way up a wall, with only one leg. Climbing down was not an option, as Hiccup needed the leg for support when climbing down so that left one option.

Jumping.

Luckily for Hiccup the jump down wasn't too far, but the fact he could only land on one leg made it rather difficult. He mentally prepared himself for the pain he was about to endure before a cry of,

"Yes, I win" from Astrid, several metres above him, throw him off and he hang onto the wall for a bit longer. "You alright Hiccup?"

"Never better Astrid, just trying to climb a wall with one fake leg and a leg was to easy, so it decided to fall off, the fake leg that is." Replied Hiccup, earning a rare giggle from Astrid at his sarcasm.

"Hold on, let me see if I can help you." Called out Astrid, she then began her descent and stopped when she was at a similar height to Hiccup.

When she was level, Hiccup explained to her that his only option was to jump and hope and on the count of three he did so, shortly follow by Astrid, leaving them laying on top of each other, with the heat from their faces radiating off each other.

Someone at the centre had seen the fall and decided that it was a good idea to embarrass the two young adults, "Aw, love on the battlefield!".

"Ew out of my way Haddock" said Astrid as she pushed her embarrassed self-off of the man beneath her, but her previously tied up hair had fallen loose and got itself under Hiccup, leaving Astrid to push Hiccup out of the way to get herself off from him.

After Hiccup had stood up and reattached himself to his leg the quartet decided that it was time for some food after a tiring sessions rock climbing.


	3. Chapter 3

**Sorry for the wait, but updates are going to be sporadic, unfortunately I have exams coming up. Thanks for the reviews people, try to keep them coming in. It really does help to motivate me to write more as well.**

 **Anyway, here's Chapter Three:**

After a tiring sessions rock climbing and the quartet spilt off into to go and have a nice warm shower and get changed into some more formal clothes to wear on the dinner out.

Hiccup and Fishlegs were finished first and found themselves waiting for the ladies by the car outside.

"So, you and Astrid. There seems to be a spark there." Claimed Fishlegs as he sat himself down into the passenger seat of Hiccup's car.

"No, there isn't, she's just being polite y'know. She wouldn't be interested in a guy like me anyway. She'd prefer someone with bulging muscles and basically everything that I'm not." Replied Hiccup

"No, she wouldn't. It's not her type, if she did don't you think Snoutlout would be here instead? And anyway, she did look genuinely worried when you lost your leg though Hiccup. And why wouldn't she be interested in you? You've got many likeable and desirable traits." To this Hiccup raised his eyebrows and questioned back,

"What traits exactly, because I don't see ques of women waiting to date the infamous one-legged man?"

"Err. Well now you've put me on the spot..." said Fishlegs

"Thanks, Fishy a real help there aren't you" replied a sarcastic Hiccup.

"Ok, I'll admit that you've got the cutest cat known to man-kind." Claimed Fishlegs.

"Great, so I can 'win' her over by introducing her to my three-legged pet?" replied Hiccup and by this time the girls were just leaving the centre and making their way towards the car.

Hiccup and Fishlegs due-fully got out of the car and opened the door for their partners. Another, "Milady" and a mock bow' from Hiccup earned him a punch to the gut from Astrid, "Why would you ever do that?" asked Hiccup, but he got no reply, only a smirk from Astrid.

After a short drive to the restaurant they all got out and began to wait to be seated. In the light you could now clearly see what everyone was wearing. Hiccup found himself in some black jeans and a tight fitting red top, Fishlegs in some brown chinos, Heather in a dark grey dress and Astrid was in a skirt with a turquoise t-shirt.

After a couple of short minutes, a young waiter with a face tattoo came and showed them a seat near the back.

"I'm Eret, son of Eret and welcome to Dragon's Edge restaurant. I'll be your waiter for tonight. We serve anything you can think of here, including a chef special, which tonight is a salted smoked eel and I must warn you, there's enough salt on it to open your own salt company." Spoke the man in a deep voice. "So, ladies and gentlemen, what would you like to drink?"

The two girls both went for white wine, Fishlegs some mead and Hiccup being the designated driver a lemonade. Eret then left and returned a bit later with there drinks.

After some awkward silence, Heather broke it by asking Hiccup, "So, how's the mayor doing?"

Heather was referring to Hiccup's father, 'Stoic the Vast' as he is known in nearby towns and by other mayors. It was a fulfilling job, but meant he had little time to spend with Hiccup when he was a kid and that Hiccup was mostly brought up by Gobber, or his godfather after the sudden passing of his mother.

"He's doing well, or as far as I know he is. He still wants me to follow in his footsteps and become mayor but it's not what I want to do." Replied Hiccup

"And what to do you want to do, Hiccup?" asked Astrid

"At the moment I'm working in Gobber's workshop as an engineer/blacksmith, but in the future, I plan on setting up my own company that specialises in building prosthetics. I mean I built my own leg, so I know I can do it." Said Hiccup as he made awkward eye contact with Astrid, who immediately realised what was happening and looked away and began twirling her long blonde hair instead in her fingers. "What are you doing now Astrid?"

"Well now that I've finished my degree, I've started to work for Berks only sports rehabilitation centres." Replied Astrid

"That sounds like cool." Said Hiccup as he continued to read the menu before making his choice for dinner. "After I lost my leg, Dr Gothi gave me lots of exercises to do and she wasn't the most motivating physiotherapist out there. It included a lot of hitting with her stick to get me to do what she wanted."

"Have you finished your physio now? Or will I be seeing you soon?" asked Astrid

"I've finished my physio now, I lost my leg a while ago."

By now Eret had came and collected are orders and told us that there would be a short wait, whilst the chefs prepare our meals.

When Eret arrived with the meals a short while later, we tucked into them. Hiccup had gone for a Spaghetti Meatballs, Astrid a juicy steak, Heather a salad and Fishlegs some yak pie.

"Wow, this is delicious, who's the chef?" asked Fishlegs to Eret, who also topped up the drinks whilst he was being questioned.

"He or it could be a she, I can't tell, is new here actually, just arrived the other day claiming to be a good Chef. Though they have this weird thing were the chef refuses to cook Chicken for some reason." Replied Eret

Instantly all four of them looked at each other and said, "Tuffnut Thorsten?"

"There's no way its him, though is there?" questioned Fishlegs, "I mean I don't know what else he'd be doing though, and he was always a good cook, but this good? No never."

"He'd probably end up worshipping Loki or something like that." Joked Hiccup. "But, I thought you'd spoken to him recently Fishlegs?"

"I didn't ask what he was doing for work, just if he could give me a hand with something." Said Fishlegs

Eret volunteered to reintroduce the old friends together and soon came back with Tuff in toe.

"Hey guys!" said an enthusiastic Tuff, whose cooking aprons were messy and could defiantly do with a clean, although it was expected that he'd be a messy chef.

"Hi Tuff, didn't know you worked here." Replied Fishlegs and the rest of the group also said hello.

"Yeah, well I just strolled in the other day and gave them some of my home baked cookies and said I wanted a job, and well here I am." Explained Tuff, who by now had pulled up a chair and joined the foursome. "What's the occasion then? Did I miss someone's birthday?" After no reply he joked, "Wait are you on a date?"

"I'm just helping Fishlegs and Heather" cleared Astrid, who looked over towards Hiccup and she could see the disappointment in his forest green eyes.

"Yeah me too" said Hiccup, with little enthusiasm in his voice.

"Ah well that's a shame you two aren't on a date" claimed Tuff, whilst gesturing to the 'wingmen', "Cos you would have super cute babies together. You can picture it can't you Fishlegs?"

"Err…um…yeah I guess they would. I mean theoretically speaking yes, they would. There gene pool is quite diverse and…" rambled Fishlegs before he was stopped by a face palm from Hiccup and a death stare from Astrid, despite a tinge of red on both of there faces. "I'm gonna stop talking now, before something worse than an Astrid death stare happens."

"Could I get a first date picture for your future wedding then? It will look good during the best man's speech?" Another deathly silence and equally deathly stare from Astrid stopped Tuff almost in his tracks, "Ah well, I'm sure you two will work it out and if not, I'll still be a massive fan of Hiccstrid."

"Hiccstrid?" asked Astrid raising her eyebrows hat Tuff

"Yeah, it's your now official ship name, just like 'Feather or Heathlegs' is the ship name for Heather and Fishlegs."

"But we're not together and won't be" said Astrid, her anger raising each time Tuff said something else about her and Hiccup.

"Yeah Tuff, its not going to happen, so drop it please, before Astrid beheads you or something" advised Hiccup, who was reeling in hurt after basically being publicly rejected in front of his friends.

"Ah well, congratulations on 'Heathlegs' and the making of 'Hiccstrid'" and with a wink Tuff went back to the kitchen and work.

Sensibly once Astrid had calmed down from the aggravation caused by Tuff, Eret arrived with the bill, which the boys duty-fully paid, despite a disagreement from Heather and Astrid.

After a short drive to Heather's, Fishlegs was also spending the night, Hiccup drove peacefully to Astrid's house. Before yet again mock-bowing and opening the car door for her and yet again earning him another punch, this time to the arm. "Do you always do that?" asked Hiccup as he began to walk her towards her doorstep.

"You know, you didn't have to walk me to the door y'know. I do know where it is, it hasn't moved in the last couple of hours." Said Astrid as she began to get her keys out of her bag.

"You're right, I didn't, but I wanted to." Causing a blush on both of their faces only hidden by the fact it was night. "Well apart from falling off a climbing wall and being questioned by Tuff, I had a good time. I hope you did too."

"I did." Replied Astrid

"Well then, maybe we could do this again sometime? Just you and me?" asked Hiccup after a brief pause, mainly to build up his courage and prepare to be rejected.

"Maybe, I'll let you know. Anyway, goodnight Hiccup" said Astrid as she punched him on the arm, before quickly brushing her hair out of her face and planted a kiss on his cheek.

By the time Hiccup realised what had just happened, Astrid had already slipped inside her house, leaving Hiccup there brushing his cheek, where Astrid's soft lips had been just moments before.


End file.
